Kind Of Like Fate
by DreamsFromADistance
Summary: SQ AU, No magic. Emma is a writer looking for inspiration. Regina recently lost her husband, leaving her and Henry to go on a planned family vacation without him. Both women sit next to each other on the plane and end up staying at the same hotel in Florida. During their stay, they grow closer, leading Emma to find her inspiration and both women to find the family that they need.
1. As Luck Would Have It

_**A/N:** So another idea hit me and I had to write it… This will be my first AU story, so I would love to hear what you think!_

 _ **Disclaimer:** I do not own OUAT, its characters, or its storylines._

 _SwanQueen AU. (No curse or magic.) Emma is a writer looking for inspiration. Regina recently lost her husband, leaving her and Henry to go on a planned family vacation without him. Both women sit next to each other on the plane and end up staying at the same hotel in Florida. During their stay, they grow closer, leading Emma to find her inspiration and both women to find the family that they both need._

* * *

 _~Kind Of Like Fate~_

 _Chapter One: As Luck Would Have It_

 _Boston Logan International Airport_

 _Y_ _ou never know what life has waiting for you around the corner._

Like literally.

Emma Swan turned the corner and had just glanced briefly to the right of her only to find herself come crashing down to the ground with two suitcases. She had also managed to take down the person standing next to those suitcases, who was talking on the phone at the exact time she tripped over the baggage.

It had been like dominos. She was the first one in the line, tipping over the first suitcase, which then tipped over the second suitcase, and finally, that suitcase tipped over the person.

And he did not look pleased at all.

At least, that was what she could tell from the now blurry world around her. Her glasses had fallen off of her face at the moment of the impact.

"What the hell?"

If his expression didn't give away his anger, his voice certainly did.

The phone had dropped from his hands and slid across the floor. And somehow her glasses had managed to projectile their way near his phone, only a few inches away from the thing. She blinked a couple of times and registered that he had also been holding a cup of coffee, which had spilled all over his business suit with the empty container and lid on the floor with the rest of them.

 _Shit._

He continued to yell at her. "Do you even watch where you're walking? Look what you've done!"

Emma scrambled to her feet and began to pick up the suitcases. "I am so, _so_ sorry." She put out her hand to help him up, but he didn't take it and instead got up on his own.

 _Asshole._

"You're lucky I have another suit, lady."

"Again, I'm really sorry. I was just in a rush to get to my gate."

"Let me guess. It's because you're late?" He shook his head in disgust as he went to retrieve his phone, but he did not bother to pick up her glasses.

 _Seriously? Show me some respect, dude. I picked up your suitcases and offered to help you up._

"Lucky you didn't break my phone either."

 _I could break that and your nose with my fist._

"Try not to be late next time, lady. That way you don't go running into people and damage their property." He held the phone back up to his ear and started talking to the person on the other end. "Sorry. Some klutz just ran into me and knocked over my things."

 _Actually, I ran into your things, which happened to knock you over._

 _Also, did I mention this guy is an asshole?_

She was glad her backpack had stayed on her shoulders during the crash. She was sure he wouldn't have picked that up for her either if it had fallen to the floor. She let out a frustrated sigh, picked up her glasses, and went on her way. She would have given the man a piece of her mind, but like he had pointed out, she was late. Very late.

Her flight was scheduled to leave out of Boston at 8:50pm. It was now 8:45. And of course, A-11, the gate where her plane was currently residing, had to be sectioned off from most of the other gates in the terminal, down a long hallway where she'd collided into those damn suitcases.

She took off in a sprint again when she was far enough away from the guy.

When she finally arrived at the waiting room, she saw that it was mostly empty and that the flight information had already changed to the next departure. She looked out the window in panic, fearful that she'd see the plane strolling away from the gate. But it was still there, and she could even see the workers throwing the last of the checked luggage on to the plane. She ran up to the check-in desk and practically threw her boarding pass at the woman, who quickly checked the ticket before handing it back to her.

"Cutting it a little close, aren't we?"

Emma refrained from rolling her eyes. She didn't need anyone else reminding her of her lateness. "Yeah."

"Have a nice trip."

She forced a smile and hurried on to the plane.

And as her crappy luck would have it, she almost stumbled into one of the flight attendants as she stepped inside the plane. She mumbled an apology to her and walked around her before she could say anything about the time. She was thankful that Southwest didn't assign specific seating, as she didn't want to waste any more time trying to figure out where she needed to sit. Once she spotted an empty seat (which to her surprise was not all the way at the back of the plane), she sat down and breathed a sigh of relief. And what was even more comforting? She had found an aisle seat, so she didn't have to cause any more commotion with the people around her since that seemed to be something she was doing a very great job at that day.

 _Alright. I'm ready for this damn thing to leave so I can just sleep until we arrive…_

"First time flying?"

Emma glanced at the woman sitting next to her, studying her expression before answering. She didn't appear to be irritated like the man she'd encountered earlier. Rather, the brunette was smiling kindly at her. And those brown eyes of hers… They were absolutely beautiful. She could get lost in those chocolate depths if she let herself. "Yeah. What gave that away?"

The woman laughed sweetly. "Hey, don't worry. I've been on flights where we waited thirty minutes after our scheduled departure time for people to show up. But you?" She glanced down at the watch on her wrist and then looked back up at her. "It's 8:50. You've made it just on time."

Emma felt herself ease up at the brunette's friendliness. "Yeah, that whole show up three hours before your flight thing?" She pulled off her backpack and pushed it under the seat in front of her. "I didn't exactly do that."

"That's definitely something you want to do. Especially nowadays."

She buckled her seatbelt and settled back into her seat. She looked back at the woman when she began to talk again.

"I'm Regina."

She put out her hand, and Emma shook it. "Emma."

"And this is my son, Henry."

Emma watched as a little brunette-haired boy peered around his mother and gave her a wide-tooth grin. "Hiya, Emma!"

"Hello, Henry. It's nice to meet you."

"It's nice to meet you, too." His green eyes flashed brightly as he asked her a question. "Are you vacationing in Florida, too?"

She smiled at his excitement. "I am. Is this your first time?"

He nodded vigorously. "I can't wait to get there. There's so much I want to do. I have a whole list and everything."

Regina smirked at Emma.

"How long is the flight again, Mom?"

"About two and a half hours."

Henry let out an exaggerated sigh. "Really? That seems like forever on a plane."

"It'll go by fast, dear. I promise."

"Okay," he said in a quiet, but unconvinced tone. He turned his attention to the window, leaning so close to it that his nose almost touched the Plexiglass surface.

Regina looked back at her and lowered her voice. "I hope you don't mind that he took the window seat. I know it's your first time flying and all…"

"It's completely fine, Regina. I can see out the window perfectly fine from here. Besides. I'll probably end up falling asleep at some point and miss anything worthwhile to see as we land."

"After we take off, he'll be out in ten minutes."

"You think so?"

"Oh, I know so. It's almost his usual bedtime, and it's been a long travel day for him."

Henry was completely oblivious to conversation they were having, his eyes still searching the outside world around the plane. Once the plane began to move and the flight attendants started explaining the safety procedures the passengers should be aware of, Regina redirected Henry's focus back to the inside of the plane. But as soon as the last word left their lips, he resumed his previous activity, surveying what was happening outside.

Cute kid.

"How old is he?" Emma asked suddenly.

"He'll be ten in three months."

It was currently July, which meant the kid had a birthday during the same month as her. "Oh? So he's got an October birthday then?"

"Yep. The twenty second, actually."

And apparently his birthday was on the same day as hers as well. "Wow, really? That's my birthday, too."

"We share a birthday?" the boy exclaimed, whipping around to face Emma with wide eyes. The very mention of his birthday had clearly piqued his interest enough to pull him away from the window.

"What a coincidence, huh?" Regina asked with a smile.

"I mean, it's only like the best birthday out there," Emma said jokingly, which earned her a nod of approval from Henry.

"Sorry, Mom. Guess you're not cool like us."

Regina pretended to be upset with this, frowning as she snapped her fingers at this sudden "realization". "Darn February birthday."

"How old are you, Emma?"

"Henry, you can't just…"

Emma interjected, putting out her hand. "It's okay. I don't mind answering that question. I'll be turning twenty eight this year."

"You're almost my mom's age. She turned thirty two this year."

The plane had begun to move again after taking a brief stop to wait for the other planes to move out of the way, and before Regina could comment on Henry sharing her age with her, he abruptly turned back to the window, wanting to view the plane's travel across the runway.

"I'm sorry about that."

Emma shook her head. "It's fine! He's curious, that's all. Especially since we happen to share the same birthday."

"He's sometimes a little too curious for his own good."

"Aren't all kids?"

The brunette chuckled. "That is very true."

Emma watched in amusement as Henry called to his mother, talking eagerly and pointing out the window as he waited in anticipation for the plane to takeoff. And if he wasn't already talking enough, he was talking nearly a mile a minute as the plane ascended into the air.

"Whoa, look at that! Mom, Mom. Look! You can see _everything_ from up here! I bet we can see our house from here."

Regina glanced at Emma, grinning.

Would this have been what her life would be like if she had a kid? Going on family trips, laughing together with the person sitting next to them on the plane, watching him get excited at the sight of the scenery below him as he looked out the plane's window…

The imagined thoughts made her eyes glistened a bit. She was glad Regina had turned back to her son, as she did not want to explain the sudden display of sadness to the woman.

That was not a topic she was willing to discuss with anyone. She didn't even like to dwell on it too long herself, otherwise she would end up losing it.

She quickly pulled the sleeve of her jacket over her hand and dabbed at her eyes before either of the two noticed anything.

Regina ended up predicting it right.

Ten minutes later, once the plane was in the air and everyone was settled down, Henry had completely passed out, his head resting against the wall next to the window. Regina looked at her and nodded her head towards him. "See? I told you he'd be out in ten minutes."

Emma smiled.

"So, Emma. What brings you to Florida?"

"Well, I lived in Tallahassee for a while before moving to Boston, and I guess I felt something pulling me back to the state. I'm hoping to find a little inspiration while I'm here."

"Inspiration?"

"I'm a writer."

"Really? I have a friend back home who's a writer, too. Well, she's aspiring to be a children's author. She's a fourth grade teacher right now, but she told me she's always had a passion for writing."

"That's really cool. You'll have to tell her good luck for me. It can be tough to get anything out there, but it's worth it in the end."

"You've gotten something published before then?"

The part about it being worth it in the end? Emma didn't really know. She imagined that having her own book finally published and out on the shelves would be something big to celebrate, but she was nowhere near that goal yet. This was why she hated telling people that she was a writer sometimes. The first instinct was always to think that she was an accomplished writer with a few award winning books out there. And why was that? Because if you weren't award winning, then you must suck at writing.

"Like _New York Times_ Best Seller?"

Regina shrugged. "Like anything."

"Does a few pieces of poetry in a magazine count?"

"I think it does!"

"Thanks, Regina. But in all actuality, I haven't had too much success. I've had a few works in the making, one draft in particular that I felt pretty good about, but after sending it out to a few publishing companies and getting rejected by _all_ of them, I knew I needed to start over. Otherwise, you may have recognized my face from the inside flap of a book cover."

"I'm so sorry to hear that, Emma. Please tell me you didn't abandon that story after all the work you put into it?"

"No, I still have it. I just need to look at it from a new perspective. That's actually what inspired this trip. I started that story back in Tallahassee, so I figured, why not come back to place where it all began?"

Regina smiled.

"The way I see it, you have to fail so many times before you succeed. Maybe while I'm here, I'll find that exact inspiration I need that will lead me to a published book in the future. So tell your friend to never give up. That if it doesn't work out at first, just take some time and rethink the story through. Because who knows? Maybe the story won't be bestselling, but maybe it will really connect with some people out there and impact their lives in a positive way."

"It sounds like you write from your heart, Emma."

"I like to think that I do."

"Well, I'll be on the lookout for your first book. Maybe even be the first in line to purchase it. But in order to do that, I'll need to know the rest of your name. Unless you write under a pseudonym, of course."

"No pseudonym. It's just Emma Swan."

"Emma Swan. I think I can remember that."

Despite the string of bad luck she'd had leading up to the flight, she found it all to be silly now if that bad luck meant her sitting next to this woman. She was so kind, and Emma never felt so comfortable with talking with someone at first glance. Making friends and talking so openly with people wasn't really something that went so well for her. She would much rather hide behind her computer and absorb herself in the world on the pages that she created than interact with the real people around her. But Regina was different. There was just that instant connection with her. And Emma didn't know if that was a good or bad thing.

Well, it was certainly a bad thing if she never got to see her again. That was the other problem. Any opportunity for a friendship or relationship with anyone always ended up slipping away from her because their stay was usually temporary. Maybe she would run into this woman and her son in Boston sometime? It was a big city, but stranger things had happened in her life before.

"So you're from Boston, too?"

Emma's heart sunk when the brunette shook her head.

 _Damn it. There goes that chance for anything. Bad luck again._

"No, actually. We're from Maine, but we were scheduled to meet up with... Um…" Emma watched the woman uneasily as she looked down for a moment. She'd caught it before she turned away. Those brown eyes glistened, and she knew something unexpected, and clearly devastating, had happened before this vacation. When Regina spoke again, her voice was quiet, and she couldn't look at her face. "Family. Because of that, I planned to have us fly out of Boston."

Emma nodded. She didn't know what else to say, not wanting to push Regina into tears about the sudden loss of a family member. At least, that's what she assumed had happened. So much for that comfortability…

But to her surprise, the hint of sadness the brunette exhibited faded as quickly as it came, as she started to laugh. Emma looked at her questioningly.

"You want to know where we're really from?"

"Now that you're laughing, I would like to."

"Seriously, you're going to get a kick out of this one."

"Why is that? The name can't be that bad."

"The name's not bad, it's just… Slightly unbelievable."

"Try me."

Along with being a writer, she was an avid reader, and the unbelievable didn't exactly faze her. She had probably come across more ridiculous names in the books she had read, and even though they were fictional names, she highly doubted that the town these two were from had a far worse name than those.

"Storybrooke."

Whoa, whoa, wait. As in a storybook? Not ridiculous, but it actually did seem unbelievable. Did they misspell storybook by adding in the "r" and the "e"? Moreover, did a group of writers name the town? That seemed highly plausible to her more than anything else.

Emma couldn't stop the look of shock on her face. "Wait… What?"

"Yep. Storybrooke, Maine."

"Okay. I know I'm a writer and would probably be more believing than most people with this one, but _Storybrooke?_ Like the town came out of a storybook? You must be joking."

Regina shook her head, laughing.

"Your friend name the town?"

"No. I swear that's the name, and everyone always thinks I've made it up to be funny."

"It is a rather unique name. I've definitely never heard of it before."

"Not many people have. It's a quaint little town. I happen to be the mayor."

"Oh, I see. So you named the town?"

The brunette smirked. "I promise you that's been the name since I was baby. And there are town records that date back years ago that show the name has been quite real for some time."

"Okay, Madam Mayor. We'll go with that."

 _Wait. Did I just call her that?_

 _Shit! Why did I say that?_

But Regina didn't comment on the name and instead grinned at her.

"Thanks for not giving me a hard time about being late, by the way."

"It's your first time flying. It's no big deal. I didn't know how to navigate an airport the first time I flew alone. Someone could tell I was a bit lost that day, so he approached me and told me all I had to do was look up." She paused, reflecting on the memory and shaking her head at what she deemed to be foolish behavior. "I was so nervous that I didn't look at the signs above me."

"Really?"

"Ha, yeah. Pretty bad, huh?"

"How old were you?"

"Twenty one. Which is even worse. Think I'd have enough common sense by then to know to follow the signs."

"If I've learned anything from today, airports are massive and even signs can lead you in the wrong direction. But hey, at least you didn't have any run-ins with anyone."

"Security give you problems?"

"No, and thank God because I may have actually missed my flight then. But I did trip over some suitcases and caused a guy to fall over and spill his coffee on himself. He was pretty pissed after that." She raised her hand in front of her mouth as soon as she registered what she had said. Henry may have been drifting in and out of sleep, and if he had heard that… "Crap. I probably shouldn't have said that so loud in front of your kid."

"Don't worry about it. I told you he's out. Watch." Regina turned to him. "Henry. First one to the room gets to have dessert for dinner for the _whole_ week."

Emma waited, but the boy never stirred.

"Pretty generous offer there."

Regina turned back to her. "Oh, I'd never let him do that. But if he was awake, he would have jumped at that one."

She grinned.

"So let me guess. This guy? He was a complete…" She lowered her voice to a whisper as a joke. "Asshole…" She raised her voice back to a normal level. "To you afterward?"

"Yes. I apologized, picked up his suitcases, and was even going to help him up but he refused my offer and got up on his own. And he was even arrogant enough to tell his buddy on the phone how much of a klutz I was."

The brunette shook her head. "Some men."

"Tell me about it."

They continued to talk for a little while more until one of the flight attendants came to their row, giving them each a small bag of pretzels and asking them if they wanted anything to drink. They both declined, neither of the two really thirsty or even hungry at the moment.

"Got to love the snacks they give you," Regina said as she placed the pretzels in a small tote bag she had under the seat in front of her.

"Midnight snack? I know I'll be hungry later."

She chuckled.

Emma decided to pull out her phone then, turning it back on after powering it down minutes before takeoff. It hadn't seemed like much time passed since leaving the airport, but it was already 9:51. She figured they had probably taken off around nine o'clock, and then there was the ten minutes of silence between the two of them… Had she really been talking with this woman for nearly forty minutes? This had to have been the longest conversation she had with someone she'd just met.

She was beginning to hit a wall, though. It would be a matter of minutes before she resembled Henry.

"Hey, Regina? Do you mind if I close my eyes for a while?"

"No, no, of course not! I'm sorry. I know I talk a lot…"

Emma shook her head. "It's okay. I've really enjoyed this. Us talking. I'm just starting to get tired."

"Please don't let me keep you. If you want to sleep, that's okay with me."

"Thanks." She leaned back slightly in her chair, trying to get comfortable.

"And Emma?"

She turned her head to look at her.

"Thank you for this conversation. I really enjoyed it, too."

Emma nodded before turning her head away and closing her eyes. She felt herself drifting rather quickly, the sounds of the airplane soon disappearing until her head began to fall forward, causing her to open her eyes and snap back to life almost instantly. She glanced around her, seeing that Regina now had her own glasses on and was reading a book on her Kindle. The scene made her smile, and she found herself settling back into sleep.

The same thing happened to her again.

She was tempted to pull the tray table down and rest her head on that instead. But she figured she would look rather odd doing that, so she did the best she could to reposition her head and closed her eyes.

A few minutes later, she heard Regina's voice.

"You can rest your head on my shoulder."

The brunette had clearly noticed her struggle to stay asleep. Emma opened her eyes and glanced at her. There was that kind smile again. Beautiful brown eyes staring into her green ones. She had known this woman for a little over an hour, and she was offering for her to rest her head on her shoulder as she slept. The gesture was so nice, but it made her feel somewhat uneasy. Wasn't that rather… Intimate? Or at least reserved for family members?

Emma really did want to rest her head on Regina's shoulder, though. Be close to her, breathe in her warm scent…

 _Emma! Why are you thinking this? She's attractive, sure, but you just met her. Plus, you're never going to see her again after tonight, so don't even indulge yourself!_

"It's okay. Really. I'll be fine like this."

Regina was persistent, though.

"You're never going to fall asleep. Trust me. I've been on enough flights to know. You'll almost fall asleep, and then your head will start to roll to the side or fall forward and you'll open your eyes, having to change positions to get comfortable again." She smirked. "Kind of like what's been happening already."

"Yeah…"

She patted her shoulder. "Go ahead, Emma. I don't mind."

 _Emma, don't…_

But how she could argue with her? Especially as those brown eyes of hers continued to stare at her?

Her lips turned upward into a smile.

"Thanks, Regina."

Emma let her head fall on the woman's shoulder, and she slowly closed her eyes.

"Emma?"

"Hm?"

"Glasses, dear. You don't want them on, do you?"

 _Dear._ She heard the brunette say the nickname once to her son, but hearing her say it now to her made her heart flutter. She quickly opened her eyes and reached up to take her glasses off, but Regina caught her hand and stopped her. The touch caused her heart to pound even more.

"I got them. You just worry about sleeping. I promise to keep them safe. I'll put them with mine."

"Okay."

She leaned back, letting Regina take off her own glasses and store both of theirs safely away. When she settled back in her seat, Emma rested her head back on her shoulder.

"I'll wake you before we land."

"Thank you again, Regina."

"Of course, Emma."

And she finally fell asleep, the slight smell of apples and cinnamon from the woman's perfume relaxing her into a pleasant sleep.

Regina didn't wake her. The woman ended up resting her head on top of hers and falling asleep herself. It was only when the pilot announced that they'd be landing soon that both of them jolted awake. They glanced at each other sleepily and backed away. They waited for the pilot to finish before they said anything.

When Regina looked back at her, her cheeks were a slight tinge of red. "Um… I guess I was tired, too."

Emma bit the tip of her fingernail and grinned.

"I should probably wake Henry." The brunette began to turn away, but she stopped suddenly and went for her bag. "Your glasses. You probably want them back."

"I mean, living in the blurry world isn't always so bad."

She laughed nervously as she brought the bag closer to her. Once she found her glasses, she held them out to her, and Emma saw that her hand was shaking slightly. She took them quickly, and the woman immediately pulled her hand away.

 _She's actually nervous._

 _She wanted me to rest my head on her shoulder because…_

 _Because she feels something, too._

 _That instant connection. She felt it just like I did._

She adjusted her glasses and fell back into her seat, unable to keep the smile from forming upon her lips.

"Wha…?" Henry rubbed his eyes and yawned. "Wait. We're almost there?"

Regina nodded. "We'll be landing in a few minutes."

"Really?" He bounced in his seat. "Awesome! Emma, Emma, did you hear that?"

Emma looked in his direction, noticing that Regina was avoiding her eyes. "I did, Henry."

"I can't believe we're almost there!" He turned to the window, talking with so much energy as he filled them in on what he saw. It was almost hard to believe that he had woken up only moments ago.

And then came the landing.

Emma gripped the armrests when the wheels first made contact with the ground, so tightly that her knuckles turned white. Regina looked her way at that exact moment and must have read the panic on her face, as she took hold of her hand.

"Hey. It's okay."

Emma squeezed her hand as the wheels hit the ground fully this time, screeching loudly as the pilot began to brake.

"I promise. It'll be okay."

She let out a shaky breath.

"Almost over, dear."

When the plane finally came to a halt, some of the passengers clapped. Emma turned to look at Regina with a frown.

"They're usually that rough."

"And people applaud that?"

Henry giggled.

She faced him with a serious stare. "How did that not scare you, kid?"

He shrugged. "I dunno. I guess I was too busy looking outside."

"I think that would have made it worse for me." She shuddered at the thought of watching the scene unfold before her.

Regina squeezed her hand gently. "The first one's always the worst since you don't know what to expect. It'll be better next time." She smiled. "Just think of me when you land back in Boston."

Emma's heart skipped a beat at her suggestion.

 _I'll be thinking of you more than just then…_

The brunette pulled her hand away, reaching for her bag as the plane began its trek towards their gate.

 _No, no, no!_

 _Her hand fits perfectly around mine…_

Emma gave Regina a weak smile when she glanced back at her.

 _Why do you have to go?_

 _There's a connection between us. You know it!_

Regina smiled at her before looking towards Henry, who had started to talk excitedly again.

 _Why does this always happen to me?_

 _Why do I always end up forming a connection with someone who leaves me?_

Not that this was Regina's fault. It was Emma's own fault for even letting herself feel any connection with her. She tuned out the two's conversation, and she tried to forget that last two and a half hours of her life.

The two and a half most wonderful hours she'd had for a while in her life.

 _What a way to start my trip._

Once they got off the plane, Regina invited her to walk with them on their way to baggage claim since they would both be heading that way.

Emma couldn't help herself. "Need someone to help you with following the signs?"

The brunette grinned. "Yeah. Something like that."

They went on their way, looking up at the signs every so often to check that they were in fact going in the right direction. They made it to baggage claim successfully, retrieving all of their luggage without any problems. Emma further accompanied them when they went to get the cars they would be renting on the trip. She even decided to take over wheeling Henry's suitcase when she noticed he was falling behind.

"Here, kid. I've got it."

Regina looked at her. "Oh, Emma, you don't…"

"It's no problem." She took the handle of his suitcase. "I can tell you're pretty tired, Henry."

He stepped away from the suitcase. "Thanks, Emma."

She nodded at him. Regina smiled in gratitude at her.

By the time they had both gotten their cars and were in the parking lot, Henry was dragging his feet. Emma joined the two by their car, helping them with putting their suitcases in the trunk.

"Bye, Emma," Henry said as he opened his door, waving sleepily at her before jumping inside.

"Bye, Henry."

Regina chuckled at his behavior, shaking her head as she closed the trunk. She turned to her, fumbling with the car keys in her hand. "Well, I guess this is it."

She tried her best not to look disappointed. "Yeah."

"It was really great to get to know you, Emma. I wish you the best with your writing. I do hope you find that inspiration you're looking for."

 _I hope so, too._ "Thanks, Regina."

The brunette smiled. "Goodnight, Emma."

"Goodnight, Regina."

And with that, she walked away.

But she wasn't ready to let go. Not just yet.

Maybe…

She stopped and turned around abruptly. "Regina?"

The woman was just about to get in her car, but she popped her head over the side and looked up expectedly.

 _Ask her for her number._

 _It won't hurt, right?_

She shifted uncomfortably. "Um…"

"Yes, Emma?"

 _Just ask!_

She opened her mouth, but she couldn't bring herself to ask the question. She settled for the easier option instead. "Have a good trip."

"You too, Emma."

She gave her a quick nod and hurried to her own car. As soon as she slid in the driver's seat, she pounded her fists on the sides of the steering wheel. "Damn it, Emma Swan. You just blew your chance. Way to go." She shook her head. "Why the fuck am I always so shy around people?"

She hadn't been shy around Regina, though. She was just scared to act on her feelings.

And things had really felt right with her. She could be herself around her.

When Emma arrived at the hotel, she was completely disheartened and couldn't wait to just end her day.

But then she heard a familiar voice.

She glanced behind her, and she felt the world melt around her.

 _Regina._

The woman was approaching her in the lobby, her half asleep son walking beside her.

"Emma?"

"Regina?"

"You're staying here?"

"No, I'm staying at the hotel next to here. I just wanted to get a feel for the other places around me, so I decided, why not walk around the lobbies to judge whether I'd made a good choice in hotel?"

The brunette laughed.

Henry tugged on his mother's hand, too tired to say anything about running into her again. "Mom, can we go to the room? Please?"

"Yes, dear." She smiled at Emma. "Guess we'll be joining each other in the elevator?"

"I suppose we will."

They headed to the elevator. Henry leaned against the wall and immediately closed his eyes.

"What floor, Emma?"

"Three."

Regina gave her a disbelieving look. "Are you serious?"

"Um… That's what my key says."

She shook her head. "We're staying on that floor, too."

"Oh. Wow. What a coincidence."

"It really is."

"It would be even more of a coincidence if we happened to be staying in the same room. Weird and kind of creepy coincidence, but a coincidence nonetheless."

"I'd almost believe anything after tonight."

Emma held up her key. "302?"

"Well, looks like the hotel didn't try to shove two parties together. But we're very close to each other. We're in room 308."

"Right down the hall, then."

Regina smiled. "Yeah. Right down the hall." When they got off the elevator, she gave Henry the key and let him go open the door to their room while she lingered in the hallway with her. "So…"

"So…"

"I assume we'll be seeing more of each other?"

"Probably."

"Well…"

"Goodnight for real this time?"

"That, and…" She glanced away briefly and then looked back up at her when she'd found her words. "Don't be a stranger. Feel free to stop by and visit us. We enjoyed your company today."

"So I take it that means I'll see you around then?"

She beamed, her brown eyes glowing with happiness. "Yes."

"Goodnight again, Regina."

"Goodnight again, Emma."

And in that moment, as she watched her walk down the hall and wave at her before she went inside her room, she knew there was a reason why neither of them had said goodbye to each other at the airport. It was never meant to be a goodbye. Rather, it was a mere hello, a start to something…

Well, she didn't know what yet, but she could wait patiently for it.

Emma rolled her suitcase to her room, smiling wide.

 _What a coincidence._

Maybe she didn't have as bad of luck as she originally thought.

She walked inside the room and went straight for the bed, collapsing on to it and gazing up at the ceiling above her. She closed her eyes for a few minutes, thinking over all of the crazy events that had led up to this evening's end.

"I can't wait for the rest of this vacation."

* * *

 _Should I continue? Leave a review and let me know what you think :)_


	2. Don't Be a Stranger

_**A/N:**_ _Hello everyone! Thank you for all of the reviews, favorites, and follows so far! I apologize that it took so long to get a second chapter up. I had a lot of ideas for how to do this chapter and rewrote it several times. I hope you like how it turned out! This one will reveal Regina's backstory._

* * *

 _Chapter Two: Don't Be a Stranger_

 _Don't be a stranger._

Those words, her beautiful smile, the way her brown eyes shone with happiness when she said she would see her around… Emma couldn't get any of it out of her mind. She tossed and turned all night, impatient to start the next day. She was thankful to hear her alarm go off, and for once, she didn't hit the snooze button.

She hurried to grab her journal and headed to the porch to watch the sunrise.

 _xxxxxx_

 _July 15, 2011_

 _You never know what life has waiting for you around the corner._

 _Like suitcases to trip over._

 _Or a man who is too arrogant to accept a helping hand after crashing into his things._

 _Or a kind woman with an adorable son who lets you rest your head on her shoulder after an exhausting day and happens to not only be vacationing in the same place as you, but is also staying at the same hotel as you. Only a few rooms over, actually._

 _How one sentence can make your heart flutter all night._

 _Don't be a stranger._

 _And that was one day._

 _Life certainly has a lot of surprises for you, doesn't it?_

 _xxxxxx_

Emma fell back into her chair, pulling her knees close to her chest. She twirled the pen in her hand, thinking over the previous day's events and imagining the moments to come that she would be able to spend with the brunette.

 _Should I go see her today? And what time?_

 _Would that be weird that I stopped by today? Too eager?_

 _She said don't be a stranger. She wants to see me again._

 _Ask her to go to breakfast? Join her at the beach? Maybe she and Henry would like to go to the little downtown area near the hotel with me this evening?_

 _No. That's too much, right? I can't overstep my boundaries. I have to remember that this is a family vacation for them. Regina meant to stop by the room and visit with them a few times. That's all._

 _Right?_

Emma let out a breath.

 _I'm a writer. Shouldn't I be able to interpret the meaning of her message?_

 _Regina's not a book, Emma. She's a person. And people are more complex than a book will ever be._

She rested her head on her knees and continued to watch the sun rise above the ocean.

 _I like her, and I want something with her. I just don't know how to go about it._

* * *

Fort Myers Beach, Florida.

Many months were spent researching for a place to vacation in Florida. Her sister offered input, too, since she had lived in the state for a couple of years now. After much consideration, a final decision was reached, the hotel was picked, and the flight was booked.

Her, Daniel, and Henry.

A two week family vacation.

The three of them had been overjoyed.

Regina couldn't help herself that night. When she went to her room and settled into bed after the long travel day, she found herself crying. The emptiness came back to her at the sight of not seeing her husband lying beside her.

He died three months ago.

She booked the flight on a Sunday night after they had all finished dinner. She remembered turning away from the computer and looking up at Daniel with a huge smile. Henry had been jumping up and down in excitement. The minute she stood up from her chair, he pulled both her and Daniel into a hug. When he backed away from the embrace, he started talking about all of the things he wanted to do. They listened happily as he chatted away.

Monday night. Seven thirty.

It was a later night at work for Daniel.

Henry was watching cartoons. She had just finished dinner and was bringing everything to the table. Daniel was supposed to be home in a few minutes' time.

Then phone rang.

And she heard the last news she ever expected to hear.

Their food went cold that night.

They rushed to the hospital immediately. Storybrooke was a small town, and the hospital was only a ten minutes' drive from their house.

Daniel had been involved in a terrible car crash. It hadn't been his fault. A drunk driver had hit him.

The doctors did everything they could, but he didn't make it. He was pronounced dead at 8:05pm.

Henry was a complete wreck. He screamed at the doctors when he heard the news. He claimed that they were lying. He didn't want to believe his father was dead. He said he couldn't be, not after they had booked their flight the night before. Not when they were supposed to go on a vacation together so soon.

When Regina went to pull him into a hug and comfort him, he pushed back at her and ran away. She said a few words to the doctor who had given them the news and hurried to follow him. She found him outside the main doors to the hospital, hunched over and sitting on ground. He was bawling like a baby. As soon as she sat down next to him, he leaned against her and cried into her shoulder. She wrapped her arms around him and rocked him gently, singing softly in his ear until he calmed down.

Mary Margaret and David Nolan found them sitting there. David was the sheriff of Storybrooke and was dealing with business on the other end of town when he received a dispatch about the crash. He drove home right away to pick up his wife and came to the hospital. The Nolans were very close friends of theirs, and the news was a devastating blow to them as well.

She was so damn grateful for their support. Without them, she didn't know if she would have be able to hold it together in front of Henry.

Regina didn't want to go into that room. She didn't want it to be real. As she walked down the hallway with Henry to Daniel's room, she considered the possibility that maybe the doctors were wrong, that maybe when they were outside, a miracle of sorts had happened and he'd come back. That he would be alive. That the three of them could still go on that trip, but they would just push the vacation forward so he could take the time he needed to recover. Even hoping against all odds that the crash had occurred. Rather, it was just some terrible nightmare, and in a few minutes, or even seconds, she would wake up to him sleeping peacefully next to her.

But she knew better.

Before they walked inside the room, she tried the best she could to prepare Henry for what he was about to see while also mentally preparing herself. Despite it all, it didn't make it any easier when they saw him, especially with knowing he was dead. How could anyone honestly prepare themselves for a moment like this?

Regina never said goodbye to Daniel. Not even at his funeral a week later. Saying goodbye meant he was gone. That she had truly lost him. And she didn't want to think that way.

They stayed at the Nolans' loft that night. She didn't want to go home right away. Not without him. It didn't feel right.

Once she knew Henry was sound asleep, she finally broke down. She had come down the stairs and only taken a few steps into the kitchen when she completely lost it. Mary Margaret rushed to her side immediately and caught her in her arms as she fell to the floor and weeped. She remembered everything going out of focus around her, struggling to control her breathing, and even getting sick at one point because she had been crying so hard. She unfortunately woke Henry up, but before he could see the state she was in, David came to her rescue and helped him fall back to sleep. She never woke him again that night, but it took several hours before she had calmed down enough to fall asleep herself. Mary Margaret ended up staying with her all night. She even called off work the next few days to watch over her and Henry. When her crying had subsided, she looked on with weary eyes as the woman filled out her substitute teaching plans for the days she would miss. It was just beginning to get light outside when she finally closed her eyes.

Mary Margaret was her rock in the time after Daniel's death. She helped her stay strong in the weeks leading up to their vacation. She had really wanted to cancel the trip. She didn't think she would be able to handle going without Daniel. But she couldn't do that to Henry. She knew how much he had been looking forward to it. Despite what had happened, he still wanted to go.

And now, here she was, day one of the vacation. It was early morning, a little after eight o'clock. She was walking the beach with Henry. Even though he had stayed up way past his bedtime the previous night, he had woken up before her and practically pulled her out of bed so they could head out.

She wasn't going to have to ask him what he wanted to do that day. She already knew they would be spending a good amount of time at the beach.

Regina smiled at Henry as he bent down and inspected another seashell.

"Mom! Look at this one!"

He was having a ball searching the beach for shells. She was certain he would have quite the collection of them by the end of their trip.

As she waited for him to look at the other shells around him, she felt a tap on her shoulder. She glanced behind her and immediately felt a wave of happiness wash through her.

 _Emma._

The blonde gave her a quick wave and joined her at her side. "Hey."

"Hello, Emma."

"Mind if I join you two?"

"Not at all." She nudged her shoulder gently. "I did say not be a stranger, after all."

Emma looked away shyly at the comment. The reaction made her own heart skip a beat.

 _God, she's so adorable._

It was her turn to look away shyly.

 _Wait. Did I just say that?_

She was thankful for the distraction when Henry jumped up from his spot and noticed Emma's arrival. "Emma!"

"Hello, Henry."

He held up the small bag of the shells he had collected. "Look at the shells I found!"

"Wow, kid. You've got a lot already."

"Yep!"

Regina watched as Emma looked at the sand for a few seconds and then knelt down on her knees. "Think you could find a shell for me if I showed you what it looked like?"

Henry nodded vigorously.

She picked up a small, pointed fragment that Regina guessed formerly belonged to a much larger shell. She held it up for him to see. "This is the top to a fighting conch shell. They can be hard to find completely whole, but judging by the shells you've collected so far, it looks like you have pretty a good eye for finding some nice shells. I bet you'll be able find a whole one of these."

"You think so?"

Emma nodded.

"Can I have that piece as a reference?"

"Yep."

Henry took the piece in his hand. "Thanks, Emma."

She stood up and brushed the sand off her legs. "Just make sure there's nothing in it. Sometimes you'll find one and see the snail inside it. You can't keep those ones. You're not allowed to take any shells with living creatures in them."

"Got it." He smiled at her and then was on his way, determined to find the shell Emma had told him about. They watched him in amusement as he ran a few paces ahead of them, all the while keeping his head down to look at the shells beneath him. Regina knew he would be preoccupied for some time.

"Collect a lot of shells back in Tallahassee?"

Emma turned to her. "Yeah. I loved learning about all the different shells and going to the beach to search for them whenever I got the chance. I had quite the collection." She laughed at herself. "I actually filled up this entire lamp base with them. And this base was like a good three feet tall. That lamp came with me to Boston. I could not leave it behind when I moved."

"It sounds like a rather unique piece of furniture. I wouldn't leave it behind either. Have a fighting conch shell in there?"

"I think I do, but there are _a ton_ of shells in that base. And it was many years ago that I filled it. I can't exactly remember if I placed one of those in it."

"Well, you've given Henry quite the mission. You won't leave without a whole one. He'll make sure to find one for you."

"Let him keep them for himself. I've found them before. They'll be a nice souvenir for him to remember his first trip to Florida by. And speaking of first times… What about you? Ever been to Florida before?"

Regina shook her head. "Nope. This is my first time, too."

"You'll like it here. A friend of mine recommended the area while I was living in Tallahassee, and I came down here a few times."

"So I guess you can be my tour guide then?"

Emma looked away briefly and then smiled at her. "I think I can do that." She put her hands in her shorts pockets and rocked on her heels before speaking again. "Going to the beach later?"

"I am. You?"

"Yep. And I imagine we'll run into each other there?"

"Most likely. It seems running into each other is something we're very good at."

"Yeah. What are the odds of this whole situation? I would have never guessed that the person sitting next to me on my flight would end up at the same hotel as me."

"And on the same floor."

"That too."

"I'm glad, though. I really did enjoy talking to you on the plane, Emma."

"I did, too."

Regina really meant it when she told Emma she enjoyed the conversation they had shared on the plane yesterday. That time that she talked with her… She needed it. She knew Henry would fall asleep after takeoff, and she had feared those quiet moments alone if the person sitting next to didn't want to talk with her. That silence would invite her mind to drift. She would start thinking about Daniel and how he should have been sitting next to her and how it wasn't fair that had died that Monday three months ago and the tears would start to come. But Emma sat next to her, they began to talk, and all that fear faded away.

She couldn't believe she had let herself rest her head on top of the blonde's and fallen asleep. She hadn't meant to fall asleep. She just wanted to close her eyes for a few minutes…

Even though she had been embarrassed by the action, she couldn't ignore the fact that she had enjoyed the closeness with her as well. And she knew she shouldn't feel that way, but she couldn't help herself. She felt something for Emma. It didn't take her long to recognize this after she had finished talking with her and allowed her to rest her head on her shoulder as she slept. She felt an instant connection with her, the same kind she had felt with Daniel when she first met him.

It made her somewhat uneasy. She wasn't sure it was right to feel that way about someone so soon after her husband's death. Or if Henry would even approve if she did act on her feelings during this vacation. But ignoring those feelings and forgetting that plane ride together? She knew she wouldn't be able to do to either of those things.

So she asked Emma not to be a stranger and well, she would see where it went from there.

"Let's not run into each other at the beach today," Regina said suddenly. "How about you come with us?"

"I couldn't impose."

"It's not imposing if I asked you to come. Besides. I know Henry would be happy if you came along. And…" She shuffled her feet in the sand. "I'd be happy too if you joined."

A smile appeared instantly on Emma's face. "Okay. What time should I be ready?"

"Sometime between eleven thirty and noon? I can call you when we're close to being ready if you, um, don't mind exchanging numbers."

Regina noticed Emma's green eyes light up at the suggestion. "I don't mind."

"Okay."

They both pulled out their cell phones and quickly exchanged numbers before turning to look at Henry, who was now sitting in the sand near the shore and intently analyzing what looked like every single shell around him.

"Want to try looking for that shell for a bit?" Emma asked.

The answer came easily. "I'd love to."

They walked over to Henry, sat down in the sand next to him, and began searching away.

* * *

Emma couldn't believe she had decided to go walking along the beach at the same time Regina and Henry had. Although, it really shouldn't have been that surprising to her, given the events of the previous day.

Like Regina had said, running into each other seemed to be something they were pretty good at doing.

Shelling was one of her favorite pastimes when she lived in Tallahassee, and she had been looking forward to partaking in it again during her vacation. But in that moment, she was completely distracted. She was thinking about the day ahead of her, when she got to spend time at the beach with Regina and Henry.

She also kept catching Regina's eyes any time she glanced up from the sand. Like it was seriously every single time she looked up. Not that she didn't like that, but it was making her heart flutter like crazy.

Emma wouldn't have spotted the conch shell had it been placed in the sand right in front of her.

 _Sorry, Henry. I'm of no use with helping you find shells today._

Henry was excited to hear that she would be joining them later. He told her they could continue what he called "Operation Fighting Conch Shell". When they headed back to their rooms, Regina explained to her that Henry had a thing for operation names.

"I can only imagine the number of operations he'll have going if I ask him to find any more shells for me."

Regina laughed.

They were now in the elevator and had just arrived on their floor. Regina gave Henry the key, and he ran off to the room with his bag of shells in his hand.

"You'll want to clean those shells," Emma told the brunette. "And check to make sure he didn't accidentally take anything live."

"We wouldn't want that, now would we?"

"Definitely not."

She pulled out her phone and glanced at the time. It was almost ten o'clock. "So, I'll hear from you in like an hour or so?"

"Yep."

"Sounds good. I'll see you later, Regina."

"See you, Emma."

Regina began to walk down the hallway when Emma noticed something.

"Regina?"

The brunette turned around. "Yes?"

She grinned and pointed at her shorts. "You, um… You still have sand on your butt."

Her brown eyes widened, and she put her hands on her hips.

"Like, I'm serious."

Regina glanced behind her and quickly brushed off the last of the sand. When she faced her again, she had an eyebrow raised.

"What?" Emma asked nervously.

"You were staring at my ass, Miss Swan."

"Hey, you remembered my last name!"

"Avoiding the subject, Miss Swan."

She bit her lip and looked down. "So… Um… Later?"

"Yes. Later."

Emma looked up hesitantly and was relieved to see the brunette grinning at her.

 _There goes the fluttering again._

 _Actually, more like pounding. And I swear she's going to hear it if I don't leave now._

"Bye, Regina."

"Goodbye, Emma."

* * *

 _She was staring at my ass._

Regina let out a chuckle once she saw Emma walk inside her room. And the blonde struggled a bit with that, having to try her key three times before successfully opening the door. She loved how nervous and awkward she could be.

She headed to her own room.

Dare she admit it….

 _I definitely looked at her ass, too._

Regina felt connected to Emma, _and_ she was attracted to her.

Could it be possible that she was ready to move on?

She still felt it was too soon, though, and she had cried last night.

She let out a breath.

 _Baby steps, Regina. It's okay to feel something for her. Just take it slow and see how you feel down the road._

 _Remember. Don't be a stranger, and see where that takes you._

* * *

 _Thoughts? I always appreciate feedback :) Promise the next update will be much sooner!_


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